1-adamantanyl-bis(methoxycarbonyl)piperidine | 839721-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-adamantanyl-bis(methoxycarbonyl)piperidine
• 英文别名: Dimethyl 1-(1-adamantyl)piperidine-4,4-dicarboxylate
• CAS: 839721-89-0
• 化学式: C₁₉H₂₉NO₄
• 分子量: 335.444
• InChiKey: INUVZXKEOCUBLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-adamantanyl-bis(methoxycarbonyl)piperidine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1-Adamantan-1-yl-piperidine-4,4-dicarboxylic acid methyl ester
  参考文献：
  名称：

  Concise synthetic strategy toward cyclic α,α-disubstituted α-amino acids bearing a δ-nitrogen atom: chiral 1-substituted 4-aminopiperidine-4-carboxylic acids

  摘要：

  A concise synthetic strategy toward cyclic alpha,alpha-disubstituted alpha-amino acids, 1-substituted 4-aminopiperidine-4-carboxylic acids have been developed. The synthetic route is a reductive amination of dimethyl bis(dioxoianemethyl)malonate with various amines, followed by Curtius rearrangement. This synthetic route is capable of synthesizing 4-aminopiperidine-4-carboxylic acids bearing a bulky substituent and optically active ones bearing a pendent chiral substituent, by the change of condensed amines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.004
• 作为产物：
  描述：

  dimethyl 2,2-bis((1,3-dioxolan-2-yl)methyl)malonate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 1-adamantanyl-bis(methoxycarbonyl)piperidine
  参考文献：
  名称：

  Concise synthetic strategy toward cyclic α,α-disubstituted α-amino acids bearing a δ-nitrogen atom: chiral 1-substituted 4-aminopiperidine-4-carboxylic acids

  摘要：

  A concise synthetic strategy toward cyclic alpha,alpha-disubstituted alpha-amino acids, 1-substituted 4-aminopiperidine-4-carboxylic acids have been developed. The synthetic route is a reductive amination of dimethyl bis(dioxoianemethyl)malonate with various amines, followed by Curtius rearrangement. This synthetic route is capable of synthesizing 4-aminopiperidine-4-carboxylic acids bearing a bulky substituent and optically active ones bearing a pendent chiral substituent, by the change of condensed amines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.004